Sadly, part of the reason for people not encrypting their email is that they believe all encryption standards to be broken. Having seen several forensic analysis software suites with options to decrypt PGP, I doubt PGP's effectiveness in keeping out unwanted eyes. I wish this were not the case. I am aware of the many news stories where encryption was hailed as preventing evidence from being gathered but I doubt that just the encryption was the problem.
On the one hand you have the fact that encryption is not integrated into email for everyone, and the other you have the lack of trust in a truly unbreakable encryption standard. You'd need both to happen to convince the masses to switch to encrypted emails.
As an alternative to keeping a copy of your current passwords around on paper, do what I do. Encrypt your passwords using conventional encryption using either PGP or GPG, either one is great. Encrypt your passwords to this conventional encryption with the answer to a question as the passphrase. The question should be one that only your coworkers or wife will know the answer to. (This in itself is simple on both windows and linux so I will refrain from explanation, there are instructions that come with both pgp and gpg)
To enable your coworkers etc to find out that you have hidden your passwords thus in the event of your death, write in your will that you have encrypted your passwords and that to decrypt the passphrase is the answer to a question. Then write the question in the will. Be sure the question has only one answer, which can be found without trying mutiliple different ways of capitalizing words. This prevents your lawyer from attempting to gain entry or get nosy, and it keeps your coworkers out of your files while you are still alive.
Everytime you change your passwords, encrypt them with the same passphrase as the answer to the question in the will, and send the encrypted text at the end of your emails to people. To solve the issue with pr0n that some of you seem to have, I suggest you place all of your sensitive data inside an encrypted partition of your harddrive that you can make using pgp or gpg. This partition will only be accessible to you and anyone else you deem should know about it. When encrypted like that you have no need to run a special delete-if-not-accessed-by script. If you do not personaly tell anyone the passphrase, then no one will even know it exsists at all unless you name it something like 'my porn'. Even then, no one can get in without the passphrase so your butt is covered.. even though you are dead.
No scary "I'm dead this is my password" messages, no need to constantly update your will with your new passwords, and no need to have a porn buddy to cover up your secret stash if you die. Just make sure that you keep your current passwords in a file someplace just like you said they would be in your will. A personal blog works great, just tell them to look through it for your encrypted post or you can send it to your trusted friends at the ends of your messages and leave them to guess what it is.
As long as you keep your passwords up to date in the encrypted text, and you make sure the text is saved by your friends or online, this method is as secretive as you want it to be, no one needs to know that you are hiding pr0n or that you are preparing for your possible death.
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Sadly, part of the reason for people not encrypting their email is that they believe all encryption standards to be broken. Having seen several forensic analysis software suites with options to decrypt PGP, I doubt PGP's effectiveness in keeping out unwanted eyes. I wish this were not the case. I am aware of the many news stories where encryption was hailed as preventing evidence from being gathered but I doubt that just the encryption was the problem. On the one hand you have the fact that encryption is not integrated into email for everyone, and the other you have the lack of trust in a truly unbreakable encryption standard. You'd need both to happen to convince the masses to switch to encrypted emails.
As an alternative to keeping a copy of your current passwords around on paper, do what I do. Encrypt your passwords using conventional encryption using either PGP or GPG, either one is great. Encrypt your passwords to this conventional encryption with the answer to a question as the passphrase. The question should be one that only your coworkers or wife will know the answer to. (This in itself is simple on both windows and linux so I will refrain from explanation, there are instructions that come with both pgp and gpg)
To enable your coworkers etc to find out that you have hidden your passwords thus in the event of your death, write in your will that you have encrypted your passwords and that to decrypt the passphrase is the answer to a question. Then write the question in the will. Be sure the question has only one answer, which can be found without trying mutiliple different ways of capitalizing words. This prevents your lawyer from attempting to gain entry or get nosy, and it keeps your coworkers out of your files while you are still alive.
Everytime you change your passwords, encrypt them with the same passphrase as the answer to the question in the will, and send the encrypted text at the end of your emails to people. To solve the issue with pr0n that some of you seem to have, I suggest you place all of your sensitive data inside an encrypted partition of your harddrive that you can make using pgp or gpg. This partition will only be accessible to you and anyone else you deem should know about it. When encrypted like that you have no need to run a special delete-if-not-accessed-by script. If you do not personaly tell anyone the passphrase, then no one will even know it exsists at all unless you name it something like 'my porn'. Even then, no one can get in without the passphrase so your butt is covered.. even though you are dead.
No scary "I'm dead this is my password" messages, no need to constantly update your will with your new passwords, and no need to have a porn buddy to cover up your secret stash if you die. Just make sure that you keep your current passwords in a file someplace just like you said they would be in your will. A personal blog works great, just tell them to look through it for your encrypted post or you can send it to your trusted friends at the ends of your messages and leave them to guess what it is.
As long as you keep your passwords up to date in the encrypted text, and you make sure the text is saved by your friends or online, this method is as secretive as you want it to be, no one needs to know that you are hiding pr0n or that you are preparing for your possible death.